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Abstract

Metathesis of ethyl oleate, catalyzed by WCl6 and SnMe4, provided diethyl 9-octadecenedioate (the desired starting material for the synthesis of civetone) in 99% yield. Dieckmann condensation of diethyl 9-octadecenedioate gave 2-ethoxycarbonyl-9-cycloheptadecenone (63% yield), the hydrolysis-decarboxylation reaction of which yielded civetone (93%). Identification of all products was by1H nuclear magnetic resonance, infrared and mass spectroscopic data. This is the first report of the synthesis of civetone from palm oil-derived products.

Key Words  Civet - civetone - diethyl 9-octadecenedioate - 2-ethoxycarbonyl-9-cycloheptadecenone - ethyl oleate - metathesis - palm oil

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